day trip to sleepy hollow

Even though Tarrytown and Sleepy Hollow are fairly close to Manhattan (a straight shot up on the Metro North), I’ve never been. I didn’t realize just how many seasonal events take place there understandably leading up to Halloween. There’s even a special water taxi that runs between the city and Sleepy Hollow just for those couple of weekends at Halloween (for this year it was October 17 and October 24), and so M and I went up yesterday to check it out.

Definitely buy your tickets early, as both the 1PM and 3PM boats were sold out by the morning of our trip up. The ride up and back down was great, but it turns out planning your day there requires a bit more than the website lets you know. The cash bar on the boat only has chips, so it’s a great opportunity to bring your own lunch. M brought us a magnificent spread – steak sandwiches, homemade guacamole, and pumpkin muffins.

There are some great historical sites to visit when you get to Sleepy Hollow. There was a festival going on in the main street through town, but it ran that Saturday night from 5-11PM. Additionally, we found out that the Philipsburg Manor was closed during the day as they prepped for the evening Halloween festivities. We were looking forward to visiting Kykuit, the Rockefeller estate, but we learned that all tours were sold out for the day.

We walked over to the Old Dutch Church Cemetery in Sleepy Hollow, and were hoping to join with a tour group there. Nope. No such luck. These tours also require advance booking through this website, so we were only able to explore the fairly sizable cemetery on our own.

We did manage to find Washington Irving’s gravestone, pictured here. It was a lovely visit regardless. We ended the day at River Grill in Sleepy Hollow, just a short distance up Beekman Avenue from the taxi departure point. Their pumpkin martini was truly fall in a glass. If we’d had more time, we would have definitely partaken in the delicious food we kept seeing come out.

So, based on our lessons learned, here are things I’d suggest if you’re planning a visit up at some point yourself:

Always buy tickets to Kykuit and Philipsburg Manor online in advance. Not only are they cheaper (buying on-site there is an additional $2 surcharge), but you’ll avoid any last minute surprises. If it’s during the peak Halloween season, booking weeks out is suggested, so you can choose your trip up timing accordingly.

Check the official Sleepy Hollow website to see what local events are happening during your visit (such as the current local run of Nevermore), and what times they are scheduled for. Based on this, an evening visit may make more sense than a daytime one.

If you’re taking the Water Taxi up, make sure to ask the workers about the return timetable, as there is no listing either on the website or at the harbor area once you exit the boat. Also make sure to book this a few weeks in advance to ensure you can choose the time you desire. If you’re going up another weekend in the fall, check out the MTA trips to Tarrytown. It’s just a bit of a walk from the train station.

Wear flat, comfy shoes. You’ll be doing a fair amount of walking and some areas, such as the cemetery, are pretty rocky and varied terrain. (You can thank me later.)